RU2741493C2 - Conjugates of sugar with dipeptide as aromatic molecules - Google Patents

Abstract

FIELD: food industry.SUBSTANCE: invention relates to compounds and compositions for use in enhancing aroma and/or brackishness of a food product. In particular, the present invention refers to compounds of general formula (I), where R1 is specified in the patent claim, and to compositions containing them.EFFECT: conjugates of sugar with a dipeptide are proposed as aromatic molecules.12 cl, 2 tbl, 7 ex, 2 dwg

Description

The technical field to which the invention relates

The present invention relates to compounds and compositions for use in enhancing the flavor and / or salinity of foods.

State of the art

Many foods consumed today have a rich umami flavor and aroma and / or meaty flavor and aroma. The umami or meaty taste of a food product can, for example, be enhanced or enhanced by the addition of monosodium glutamate (MSG) and / or GMP and IMP ribonucleotides to their recipes separately. Many such flavor enhancers are available today and are used for a number of different culinary uses and in a number of different forms, such as pastes, powders, liquids, pressed cubes or granules.

The addition of culinary aids helps to provide palatability and enhance the flavor and aroma of foods. And, of course, all over the world, taste and aroma are perceived as one of the key characteristics of high quality food. Consequently, a lot of research is devoted to the identification and analysis of new molecules that provide palatability and enhanced flavor and aroma properties of foods.

For example, in a recent scientific publication by A. Dunkel and T. Hofmann (Dunkel and Hofmann, 2009, J. Agric. Food Chem. 2009, 57, 9867-9877), organoleptically directed fractionation of freshly cooked chicken soup in a water bath determined that a contribution to the thick β-alanyl dipeptides L-anserine, L-carnosine, and β-alanylglycine introduced acidic oresensation of white meat. As a result of quantitative analysis followed by experiments on taste recombination and omission, it was found for the first time that when they are present together with L-glutamic acid and sodium and / or potassium ions, subthreshold concentrations of these three β-alanyl peptides improve typical thick-sour oresensation and character white meat inherent in poultry meat. This is the first step in finding new compounds capable of imparting richness in flavor and enhancing the umami flavor of glutamate.

T. Sonntag et al., J. Agric. Food Chem. 2010, 58, 6341-6350 describes organoleptically directed fractionation of beef stew juice, which led to the identification of several flavoring derivatives of dipeptides and creatinine. Quantitative analysis revealed that subthreshold concentrations of these taste-modulating molecules enhance the typical thick acidity and oresensation that provides the dry mouth sensation associated with beef stew juice.

J.P. Ley, Chem. Percept. 2008, 1: 58-77 presents bitterness-masking molecules that may be useful in foods and beverages. In particular, Ley describes ornithine and ornithine derivatives such as L-ornithyl-β-alanine or L-ornithinyl taurine as having bitter masking effects against potassium salts. L-Ornithine has also been described as an off-flavor inhibitor in combination with the bitter branched chain amino acids.

M. Tamura et al. Agric. Biol. Chem., 1989, 53 (2), 319-325 describes the relationship between flavor and primary structure of an appetizing peptide from beef soup that provides salty and umami flavors as well as appetizing flavor. The authors cited earlier work in which they synthesized ornithyl taurine as an example and found that it provided a salty taste. A similar taste effect has been found with other similar dipeptides.

Disclosure of invention

The object of the present invention is to improve the prior art and provide the prior art with an alternative or improved solution, avoiding at least some of the disadvantages described above. In particular, it is an object of the present invention to provide an alternative or improved solution for enhancing the taste and aroma of food products. In particular, it is an object of the present invention to improve the taste such as, for example, the mouthwatering umami and / or salty taste of a food product. It is also an object of the present invention to improve the aroma of food products, such as, for example, meat aroma, bread aroma, and in particular grilled meat aroma or bread aroma.

The object of the present invention is achieved by the subject matter set forth in the independent claims. In the dependent claims, the idea of the present invention is further developed.

Accordingly, a first aspect of the present invention provides a compound of general formula I:

I),

I),

moreover, R1 is hydroxyl (–OH) or an acid containing an amino group, and wherein n is 1 or 2; or a salt of said compound.

In a second aspect, the present invention relates to a composition containing said compound of general formula I) in an amount of at least 0.25 mg / g, preferably at least 0.5 mg / g, 1.0 mg / g, 1.5 mg / g, 2.5 mg / g or 5 mg / g of the total composition.

Additional aspects of the present invention relate to the use of said compound for enhancing the flavor and / or salinity of a food product.

Another aspect of the present invention is a method of enhancing the flavor and / or salinity of a culinary food product, comprising the step of adding said compound or a composition containing said compound to the food product.

Surprisingly, the inventors have found that certain sugar conjugates with ornithine and ornithine dipeptides have a significantly stronger flavor enhancing effect than their corresponding aglycones. In fact, these sugar conjugates enhance the perception of grilled meat aroma and bread aroma and salty taste at significantly lower threshold levels than their respective aglycones. They also enhance the persistence of these aromas and flavors in the mouth, while at the same concentration the corresponding aglycones do not act on aromas at all in their pure form. Such sugar conjugate molecules are typically provided in situ during the thermal processing of foodstuffs by condensation of a reducing sugar, for example, with ornithine or an ornithine dipeptide such as, for example, L-ornithinyl-β-alanine or L-ornithinyl taurine. Corresponding aglycones, i.e. ornithine and ornithine dipeptides, have been identified and described, for example, Sonntag et al., 2010, J. Agric. Food Chem. 58,6341-6350; J.P. Ley, Chem. Percept. 2008, 1: 58-77; and M. Tamura et al., Agric. Biol. Chem. 1989, 53 (2), 319-325.

However, the palatability of these ornithine derivatives differs from the palatability of their corresponding sugar conjugates. Proof of this is provided in the Example section below. Thus, the molecules described in the present invention are more capable of enhancing aroma and salty taste compared to the known ornithine and ornithine dipeptides. They allow for further reductions in the amounts and uses of, for example, monosodium glutamate (MSG), ribonucleotides such as IMP and GMP, and common table salt in culinary foods and applications without compromising the richness of flavor, palatability and salinity of said foods. They also allow the creation of spicy food concentrates that contain significantly less MSG, ribonucleotides and / or salts, or none at all, while continuing to provide a strong and typical mouth-watering, meaty, salty taste effect when used in a food product. It also allows for the creation of spicy food concentrates that are stronger and more concentrated in providing grilled meat flavor or salty flavor to the food product when used.

Brief description of figures

FIG. 1 shows the sensory evaluation of chicken soups flavored with 2 g / l Fru-orn-βala (a) and orn-ala (b). The organoleptic scores of the taste / aroma indices are shown as differences (positive and negative) with the corresponding scores of the control sample of chicken soup without orn compounds. *) indicates statistically significant differences.

FIG. 2 shows the sensory evaluation of chicken soups flavored with Fru-orn at a concentration of 2 g / l (a) and 0.25 g / l (b). Taste / aroma organoleptic scores are shown as differences (positive and negative) with the corresponding scores of the control chicken soup without orn compound. *) indicates statistically significant differences.

Implementation of the invention

The present invention relates to a compound of general formula I) wherein R1 is hydroxyl (—OH) or an acid containing amino group, and wherein n is 1 or 2; or a salt of said compound. In particular, the amino-containing acid can be selected from the group consisting of alanine, taurine, aspartic acid, and glutamic acid.

When n is 1, the sugar moiety of the compound of general formula I) is preferably selected from xylose or ribose. In this case, the compound is preferably a xylose or ribose derivative.

When n is 2, the sugar moiety of the compound of general formula I) is preferably glucose. In this case, the compound is preferably a glucose derivative.

Preferably, the compound of the present invention is selected from the group consisting of 1-deoxy-D-fructosyl-N-ornithine, 1-deoxy-D-fructosyl-N-ornithyl-β-alanine, 1-deoxy-2-pentulofuranose-1-yl- ornithine and 1-deoxy-2-pentulofuranose-1-yl-ornithyl-β-alanine.

A second aspect of the present invention relates to a composition containing said compound of general formula I) in an amount of at least 0.25 mg / g, at least 0.50 mg / g, at least 0.75 mg / g, at least 1.0 mg / g, at least 1.5 mg / g, at least 1.7 mg / g, at least 2 mg / g, at least 2.5 mg / g, at least 3 mg / g, at least 3.5 mg / g, or at least 5 mg / g of the entire composition.

In one embodiment of the present invention, the composition is in the form of an extract from plant, mushroom and / or meat raw materials. Preferably, the composition is in the form of an extract, for example from plant, mushroom and / or meat raw materials, enriched with a compound of the present invention. The advantage is that the composition is of natural origin and does not contain any chemically synthesized compounds.

In another embodiment, the composition of the present invention is the result of an aromatization reaction. As used herein, the term "aromatization reaction" refers to a chemical reaction that occurs between at least one reducing sugar and at least one amino acid or protein. Typically this chemical reaction occurs during heating and is commonly referred to as the Maillard reaction. In one example, the aromatization reaction is a Maillard reaction.

In a preferred embodiment, the composition of the present invention is a food composition. By the term "food" we mean that the composition is suitable for human consumption, for example, directly, in concentrated form and / or when used in a food product in a diluted form.

For example, the composition of the present invention is selected from the group consisting of a culinary seasoning, a culinary aid, a sauce or soup concentrate, a dry or wet animal feed.

Additional aspects of the present invention relate to the use of said compound for enhancing the aroma and / or taste of a food product. Such a food product may be a ready-to-eat food product. It can also be a concentrated flavoring agent used to flavor another food product. Advantageously, the compound of the present invention can be used for addition to a seasoning, culinary aid or food concentrate. Thus, in a seasoning, culinary aid, or food concentrate, the power of providing, for example, a meaty or salty taste to another food product is increased.

In particular, the present invention also relates to the use of the compounds for enhancing the aroma of grilled meat or the aroma of bread in a food product.

In addition, the present invention also relates to the use of the compounds of the present invention for enhancing the salinity of a food product. In particular, this use will either enhance the perceived salinity of a food without actually increasing the salt or sodium level in said food, or reduce the amount of salt or sodium used in the food while maintaining the actual perceived salinity of said food. The advantage is the ability to significantly reduce the amount of salt and sodium currently consumed by consumers with such products.

Additional aspects of the present invention also relate to the use of a composition containing said compound in an amount of at least 0.25 mg / g, at least 0.50 mg / g, at least 0.75 mg / g, at least 1, 0 mg / g, at least 1.5 mg / g, at least 1.7 mg / g, at least 2 mg / g, at least 2.5 mg / g, at least 3 mg / g at least 3.5 mg / g or at least 5 mg / g of the entire composition to enhance the flavor and / or salinity of the food product. The advantage is that the food product can be a ready-to-eat food product.

Another aspect of the present invention is a method of enhancing the flavor and / or salinity of a culinary food product, comprising the step of adding said compound or a composition containing said compound to the food product. The food product can be a ready-to-eat food or a concentrated flavor.

It will be apparent to those skilled in the art that all of the elements of the present invention described herein can be freely combined. In particular, the features described with respect to the products of the present invention can be combined with the uses and method of the present invention, and vice versa. In addition, you can combine the elements described for the various embodiments of the present invention. Additional advantages and elements of the present invention will be apparent from the figures and examples.

Example 1. Synthesis or preparation of 1-deoxy-D-fructosyl-N-ornithyl-β-alanine (Fru-Orn-βala)

Stage 1. Synthesis of benzyl (S) -3- (2 - ((((9H-fluoren-9-yl) methoxy) carbonyl) amino) -5 - ((tert-butoxycarbonyl) amino) pentanamido) propanoate I

Compound No. / Reagents Qty mmol Ratio eq. Output 2 - ((((9H-Fluoren-9-yl) methoxy) carbonyl) amino) -5 - ((tert-butoxycarbonyl) amino) pentanoic acid 15.0 g 33.039 1.0 15.0 g (73.85%) Benzyl 3-aminopropanoate 20.69 g 115,638 3.5 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC. HCl) 8.20 g 42,951 1.3 Hydroxybenzotriazole (HOBT) 2.23 g 16,519 0.5 Dichloromethane 600 ml - 40 vol.

2 - ((((9H-Fluoren-9-yl) methoxy) carbonyl) amino) -5 - ((tert-butoxycarbonyl) amino) pentanoic acid (15.0 g, 33.039 mmol, 1.0 eq.) Was dissolved in dichloromethane (600 ml) followed by the addition of benzyl 3-aminopropanoate (20.69 g, 115.638 mmol, 3.5 eq.), EDC. HCl (8.20 g, 42.951 mmol, 1.3 eq.), HOBT ( 2.23 g, 16.519 mmol, 0.5 eq.) At room temperature. The resulting solution was stirred at room temperature for 5 hours. The mixture was then diluted with dichloromethane (300 ml) and washed with saturated bicarbonate solution (300 ml). The organic layer was dried over Na ₂ SO ₄ and concentrated under reduced pressure to give the crude product, which was then purified by column chromatography using 60–120 mesh neutral silica gel. 0-60% ethyl acetate was used as a gradient in hexane for elution. After evaporation of the solvent under reduced pressure, 15.0 g of compound I (73.85%) were obtained.

Stage 2. Synthesis of benzyl (S) -3- (2 - ((((9H-fluoren-9-yl) methoxy) carbonyl) amino) -5-aminopentanamido) propanoate II

Compound No. / Reagents Qty mmol Ratio eq. Output Compound I 15.0 g 24.390 1.0 11.9 g (94.74%) HCl in 1,4-dioxane (4 M) 20 ml - - Dichloromethane 300 ml - 20 vol.

Compound I (15.0 g, 24.390 mmol, 1.0 eq.) Was dissolved in dichloromethane (300 ml) and HCl in 1,4-dioxane (4 M) was slowly added at 0 ° C. The resulting mixture was stirred at room temperature for 4 hours. The reaction mass was then concentrated under reduced pressure to obtain 11.9 g of compound II (94.74%).

Stage 3. Synthesis of 3 - ((2S) -2 - ((((9H-fluoren-9-yl) methoxy) carbonyl) amino) -5 - (((2,3,4,5-tetrahydroxytetrahydro-2H-pyran -2-yl) methyl) amino) pentamido) propanoic acid III

Compound No. / Reagents Qty mmol Ratio eq. Output =
13.4 g (100%) Compound III 11.8 g 22.912 1.0 D-glucose 11.54 g 64,155 2.8 Sodium bisulfite 0.66 g 6.415 0.28 Glycerol 20 ml - - Acetic acid 7 ml - - Methanol 80 ml - - Water 80 ml

D-glucose (11.54 g, 64.155 mmol, 2.8 eq.) And sodium bisulfite (0.66 g, 6.415 mmol, 0.28 eq.) Were added to a mixture of methanol (80 ml) and glycerol (20 ml) ... The reaction mass was then refluxed for 30 min at 80 ° C, followed by the addition of compound II (11.8 g, 22.912 mmol, 1.0 eq.) And acetic acid (7 ml). The reaction mass was then heated at 100 ° C for 5 hours and concentrated under reduced pressure to obtain 13.4 g of the final compound III, which was used without any further purification.

Stage 4. Synthesis of Fru-orn-βala

Compound No. / Reagents Qty mmol Ratio eq. Output Compound III 13.4 g 22,827 1.0 4.2 g (50.42%) 10% Pd on coal (50% moisture) 4.0 g - - MeOH 400 ml - 40 vol.

Compound III (13.4 g, 22.827 mmol, 1.0 eq.) Was dissolved in MeOH (400 ml) and 10% Pd on carbon (50% humidity) was added slowly. The resulting suspension was stirred at room temperature for 6 hours under an atmosphere of H ₂ . After completion, the reaction mass was filtered through celite, washed with water and concentrated under reduced pressure to obtain 8.0 g of a crude product, which was then poured into a packed column (Amberlite IRN-77 ion exchange resin, 100 g) and eluted with 0.2% NH ₃ in water. The collected fractions were evaporated under reduced pressure to obtain 4.2 g of Fru-Orn-βαla (50.42%).

¹ H NMR spectrum in D ₂ O: 1.582-1.591 (d, 4H), 2.277-2.310 (t, 2H), 2.889-2.924 (m, 2H), 3.115-3.136 (m, 2H), 3.232-3.261 (m , 1H), 3.359-3.376 (m, 2H), 3.604-3.629 (m, 2H), 3.749-3.774 (m, 1H), 3.877-3.907 (m, 2H).

Liquid chromatography mass spectrometry was performed using a Sunfire C18 (250 x 4.6 mm, 5 μm). The flow rate in the column was 0.3 ml / min, and 0.1% TFA in water (A) and MeOH (B) were used as solvents. Elution method: isocratic 95% A and 5% B.

Molecular ion peak Wavelength Retention time Fru-Orn-βAla 366.25 [M + H] ⁺ 202 nm 10,082

Example 2. Synthesis or preparation of 1-deoxy-D-fructosyl-N-ornithine (Fru-Orn)

Stage 1. Synthesis of benzyl 5-amino-2 (((benzyloxy) carbonyl) amino) pentanoate IV

Reagents Qty mmol Ratio eq. Output Z-Orn-OH 20.0 g 75,187 1.0 17.0 g (63.5%) PTSA H ₂ O 14.28 g 75,187 1.0 Benzyl alcohol 24.36 g 225,563 3.0 Toluene 400 ml - 20 vol.

To a stirred solution of Z-Orn-OH (20.0 g, 75.187 mmol, 1.0 eq.) In toluene, at room temperature was added PTSA · H ₂ O (14.28 g, 75.187 mmol, 1.0 eq.) and benzyl alcohol (24.36 g, 225.563 mmol, 3.0 eq.) and the mixture was then stirred overnight at 120 ° C while collecting water with a Dean-Stark separator. Upon completion, the reaction mixture was cooled to 0 ° C and diluted with diethyl ether. The product was filtered and dried under reduced pressure to give 17.0 g of compound IV (63.5%).

Stage 2. Synthesis of benzyl 2 - (((benzyloxy) carbonyl) amino) -5 - (((2,3,4,5-tetrahydroxy-tetrahydro-2H-pyran-2-yl) methyl) amino) pentanoate V

Reagents Qty mmol Ratio eq. Output Glucose 22.65 g 125,842 2.8 15.8 g (67.86%) Compound IV 16.0 g 44,943 1.0 Sodium bisulfite 1.30 g 12,584 0.28 Glycerol 20 ml - - Acetic acid 5.1 ml - - Methanol 60 ml - - Water 60 ml

D-glucose (22.65 g, 125.842 mmol, 2.8 eq.) And sodium bisulfite (1.3 g, 12.584 mmol, 0.28 eq.) Were added to a mixture of methanol (60 ml) and glycerol (20 ml) ... The reaction mass was then refluxed for 30 min at 80 ° C followed by the addition of compound IV (16.0 g, 44.943 mmol, 1.0 eq.) And acetic acid (5.1 ml). The reaction mass was then heated at 80 ° C for 3 hours, cooled and diluted with water (60 ml). The mixture was then poured into a packed column (Amberlite IRN-77 ion exchange resin, 160 g). The crude product was eluted with water and the collected fractions were then evaporated under reduced pressure to give 15.8 g of pure compound V (67.86%).

Stage 3. Synthesis of Fru-orn

Reagents Qty mmol Ratio eq. Output Connection V 15.8 g 30,501 1.0 4.8 g (53.57%) 10% Pd on coal (50% moisture) 5.0 g - - MeOH 400 ml

Compound V (15.8 g, 30.501 mmol, 1.0 eq.) Was dissolved in MeOH (400 ml) and 10% Pd on carbon (50% moisture) was added slowly. The resulting mixture was stirred at room temperature overnight under an atmosphere of H ₂ . After completion, the reaction mixture was filtered through celite, washed with water and concentrated under reduced pressure. The crude product was then poured into a packed column (Amberlite IRN-77 ion exchange resin, 100 g) and eluted with 0.5% NH ₃ in water. The collected fractions were evaporated under reduced pressure to give 4.8 g of Fru-Orn (53.57%).

¹ H NMR spectrum in D ₂ O: 1.679-1.814 (m, 4H), 2.920-2.957 (t, 2H), 3.055-3.072 (d, 2H), 3.197-3.242 (t, 2H), 3.552-3.672 (m , 3H), 3.759-3.791 (m, 1H), 3.876-3.905 (d, 2H).

Liquid chromatography mass spectrometry was performed using a Sunfire C18 (250 x 4.6 mm, 5 μm). The flow rate in the column was 0.5 ml / min, and 20 mM ammonium acetate + 0.1% acetic acid in water was used as a solvent. Elution method: isocratic (100% A).

Molecular ion peak Wavelength Retention time Fru-Orn 295.10 [M + H] ⁺ 236 nm 4.710

Example 3. Synthesis or preparation of 1-deoxy-2-pentulofuranose-1-yl-ornithine (Rib-Orn)

Stage 1. Synthesis of (2S) -2 - (((benzyloxy) carbonyl) amino) -5 - ((((3R, 4R) -2,3,4-trihydroxytetrahydrofuran-2-yl) methyl) amino) pentanoic acid

I

Reagents Qty mmol Ratio eq. Output D-Ribose 22.55 g 150,375 4 10.0 g (66.66%) Carboxybenzylornithine (Z-Orn-OH) 10,0 g 35,593 1.0 Acetic acid 0.6 ml - - Methanol 800 ml - -

D-Ribose (22.55 g, 150.375 mmol, 4.0 eq.) Was suspended in methanol (800 ml). The reaction mixture was then refluxed for 60 min at 90 ° C followed by the addition of Z-Orn-OH (10.0 g, 35.593 mmol, 1.0 eq.) And ACOH (0.6 ml). The reaction mass was heated at 90 ° C for another 1 hour. Upon completion, the reaction mass was lyophilized to give the final crude compound, which was purified by precipitation in MeOH: ACN (1: 5). The solid product was lyophilized to give 10.0 g of pure compound I (66.66%).

Stage 2. Synthesis of (2S) -2-amino-5 - ((((3R, 4R) -2,3,4-trihydroxytetrahydrofuran-2-yl) methyl) amino) pentanoic acid

Reagents Qty mmol Ratio eq. Output (2S) -2 - (((Benzyloxy) carbonyl) amino) -5 - ((((3R, 4R) -2,3,4-trihydroxytetrahydrofuran-2-yl) methyl) amino) pentanoic acid (compound I) 10,0 g 25.062 1.0 4.8 g (69.69%) 10% Pd on coal (50% moisture) 4.0 g Methanol 600 ml - -

(2S) -2 - (((Benzyloxy) carbonyl) amino) -5 - ((((3R, 4R) -2,3,4-trihydroxytetrahydrofuran-2-yl) methyl) amino) pentanoic acid (compound I) ( 10.0 g, 25.062 mmol, 1.0 eq.) Was dissolved in MeOH (600 ml) and 10% PD on carbon (50% humidity) was added slowly. The resulting mixture was stirred at room temperature for 2 hours under an atmosphere of H ₂ . After completion, the reaction mixture was filtered through celite and washed with water. It was lyophilized to obtain 4.8 g of pure Rib-Orn compound (yield: 69.69%).

¹ H NMR spectrum in D ₂ O: 1.700-1.816 (m, 4H), 3.042-3.188 (m, 2H), 3.213-3.245 (m, 1H), 3.543-3.552 (m, 1H), 3.746-3.964 (m , 3H), 4.037-4.351 (m, 2H).

Liquid chromatography with mass spectrometry was performed using an X-Bridge C18 column (250 x 4.6 mm, 5 μm). The flow rate in the column was 0.5 ml / min and 10 mM ammonium acetate + 0.3% NH ₃ in water was used as a solvent. Elution method: isocratic (100% A).

Molecular ion peak Wavelength Retention time Rib-Orn 265.28 [M + H] ⁺ 202 nm 6.54

Example 4. Sensory evaluation of compounds in water

Each of the compounds (ornithine, ornithyl-β-alanine, 1-deoxy-D-fructosyl-N-ornithine, 1-deoxy-D-fructosyl-N-ornithyl-β-alanine and 1-deoxy-2-pentulofuranose-1- yl-ornithine (Rib-Orn)) was diluted with water and dissolved in it with a final concentration of 2 g / L. The solutions were then evaluated by 12 panelists, previously screened and selected for their organoleptic properties. The sensory evaluation results can be summarized as follows. Although the aqueous solution with L-ornithine was described as sweet in the literature, the aqueous solution with the dipeptide ornithyl-β-alanine was perceived as tart; an aqueous solution with 1-deoxy-D-fructosyl-N-ornithine was described as salty, and an aqueous solution with Rib-Orn was perceived as tart, sour, metallic and sweetish.

Example 5. Sensory evaluation of compounds in a chicken soup base

Sample preparation. Chicken soups were prepared by dissolving 6 g of chicken base powder (detailed recipe is shown in Table 1), 1 g of sodium glutamate and 1 g of sodium chloride in 500 ml of hot water. Then added separately 1-deoxy-D-fructosyl-N-ornithyl-β-alanine, N-ornithyl-β-alanine, 1-deoxy-D-fructosyl-N-ornithine or alternatively 1-deoxy-2-pentulo-furanose-1 -yl-ornithine (Rib-Orn) at final concentrations of 2 and 0.25 g / l.

Table 1. Composition of chicken soup base powder

Ingredient Amount (wt%) Chicken Powder thirty Starch 1.52 Flavors 2.58 Celery powder 0.50 Garlic powder 0.90 Chicken fat 8.00 Maltodextrin 56.50 In total 100

Sensory Research Protocol. Organoleptic evaluation was carried out by 12 tasters, pre-selected for their organoleptic abilities. The tasters evaluated a maximum of 6 samples per session. Vittel water and crackers were available as a mouth cleanser. In all cases, tasters were asked to rate the samples for the following indicators: overall persistence of aroma, meat aroma, grilled / popcorn aroma, bread aroma, sweetness, bitterness and salinity. Samples were randomly coded with 3-digit numbers according to a balanced presentation design, heated to about 65 ° C and exposed in 40 ml brown plastic containers under red light to minimize appearance differences (each sample yield approximately 25 ml).

Statistical analysis of the results. The following statistical tests were used to analyze the raw sensory data. First, analysis of variance (ANOVA) was performed with two factors, products (fixed factor) and subject (random factor), to determine if there was a difference between the samples. The limit of significance (alpha risk) was set at 5%. Then, to determine which pairs of samples differed significantly, for cases where ANOVA showed a significant difference, a least significant difference (LSD) test was performed with multiple pairwise comparison. The limit of significance (alpha risk) was set at 5%.

Sensory evaluation results

Comparison of control soup (REF) and soup containing N-ornithyl-β-alanine dipeptide (orn-ala)

Despite the fact that the orn-ala dipeptide was perceived as tart in aqueous solution, no statistically significant difference could be found when comparing the diluted chicken soup base with or without orn-ala dipeptide at 2 g / L. The same was true for all of the above organoleptic characteristics, i.e. overall aroma persistence, meat aroma, grilled / popcorn product aroma, bread aroma, sweetness, bitterness and salinity. This means that at a low concentration of 2 g / L of orn-ala, the dipeptide does not affect the flavor profile of a simple chicken soup base.

Comparison between soup bases containing N-ornithyl-β-alanine dipeptide (orn-ala) and sugar conjugate 1-deoxy-D-fructosyl-N-ornithyl-β-alanine (Fru-Orn-βala)

When comparing the organoleptic profile of a soup containing orn-ala dipeptide with a soup containing Fru-Orn-βala, each time at the same concentration of 2 g / liter of ornithine compounds, bitterness, bread aroma, grilled product aroma and overall aroma persistence were significantly different ... In fact, Fru-Orn-βala Sugar Conjugate significantly boosted the performance of bread and grilled food, while significantly reducing the perceived bitterness of chicken soup. The result is shown in FIG. one.

It can be concluded that the addition of the Fru-Orn-βala sugar conjugate positively alters the aroma profile of the chicken soup and enhances the desired grilled aroma and bread aroma while reducing overall bitterness when directly compared to its corresponding control orn- ala dipeptide.

Chicken soups with sugar conjugated with ornithine at various concentrations

When the glucose-ornithine conjugate, i.e. 1-deoxy-D-fructosyl-N-ornithine, was added to the chicken soup base at a concentration of 0.25 g / L and its effect on aroma was tested, the desired bread aromas were significantly more perceptible than with control soup base. However, at a higher concentration of 2 g / L, a significant increase in the aroma of the grilled meat and salinity was observed.

Notably, when the ribose-ornithine conjugate, ie Rib-Orn, was added to the chicken soup base at a concentration of 0.25 g / L, both the baked bread flavor and umami flavor were significantly enhanced over the control soup base.

It can be concluded that the addition of a sugar-ornithine conjugate alters the aroma profile of the chicken soup and especially enhances the desired grilled aroma and bread aroma, as well as the salty and savory flavor. The results are shown in FIG. 2.

Summary of Organoleptic Test Results

Table 2 summarizes the main organoleptic effects of the tested sugar conjugates.

table 2

Connections Known indicators Aroma index in water (2 g / l) Organoleptic influence on chicken soup Fru-Orn Salty Grilled / Popcorn, Bread Product, Salty Fru-Orn-βala Sweet, bread product Grilled / Popcorn, Bread Product, Salty Orn-ala Salinity enhancement effect Tart Not Orn Sweet Have not experienced Have not experienced Rib-Orn Astringent, sweetish Grilled / baked product, umami

Example 6 Comparison between Soup Bases Containing 1-Deoxy-D-fructosyl-N-Ornithine Sugar Conjugate (Fru-orn) and a Mixture of Glucose and Ornithine

The first soup was prepared by adding 2 g / L (6.82 mmol / L) 1-deoxy-D-fructosyl-N-ornithine to the above soup base. The second soup was prepared by adding the same molar concentration of glucose and ornithine. The solutions were then evaluated by 6 tasters using the same procedure as described above.

Clear differences were found between the two samples: a soup containing 1-deoxy-D-fructosyl-N-ornithine was noted to be saltier when tasted with a nose clip and had a stronger chicken flavor when tasted without a nose clip.

Example 7. Seasoning compositions

Tomato soups can be prepared by dissolving 6 g of commercially available tomato base powder in 500 ml of hot water. 1-deoxy-D-fructosyl-N-ornithine, or alternatively 1-deoxy-D-fructosyl-N-ornithyl-β-alanine, can be added to soups at a concentration of 2 g / l to improve their flavor and aroma profile. The soups will then develop a more pungent grilled flavor and will be perceived to be slightly saltier than the corresponding ornithine-free controls.

Claims (14)

1. Compound of general formula I

I), wherein R1 is hydroxyl (-OH) or β-alanine, and n is 1 or 2. 2. A compound according to claim 1, wherein the compound with n equal to 1 is a xylose or ribose derivative. 3. A compound according to claim 1, wherein the compound with n equal to 2 is a glucose derivative. 4. The compound according to claim 1, which is 1-deoxy-D-fructosyl-N-ornithine, 1-deoxy-D-fructosyl-N-ornithyl-β-alanine, 1-deoxy-2-pentulo-furanose-1-yl- ornithine or 1-deoxy-2-pentulofuranose-1-yl-ornithyl-β-alanine. 5. A composition containing a compound according to one of claims. 1-4 in an amount of at least 0.25 mg / g, preferably at least 1.5 mg / g, which is a food composition and in which the specified compound is contained to enhance the aroma and / or salinity of the food product. 6. A composition according to claim 5, selected from the group of products consisting of a culinary seasoning, culinary additive, sauce or soup concentrate, dry or wet animal feed. 7. Application of the connection according to one of paragraphs. 1-4 to enhance the flavor of the food. 8. Use of a compound according to claim 7 for enhancing the aroma of grilled meat or the aroma of bread in a food product. 9. Application of the connection according to one of paragraphs. 1-4 to enhance the salinity and / or uminess of the food. 10. The use of a composition according to one of paragraphs. 5-6 to enhance the flavor and / or salinity of the food. 11. A method of enhancing the aroma of grilled meat and / or the aroma of bread in a culinary food product, comprising the step of adding a compound according to one of claims to the food product. 1-4 or compositions according to one of paragraphs. 5-6. 12. A method of enhancing the salinity of a culinary food product, comprising the step of adding a compound according to one of claims to the food product. 1-4 or compositions according to one of paragraphs. 5-6.

Images